Tax law and fiscal policies are central to understanding the deepest values of a society: the way a state distributes wealth, mobilizes resources, and enforces the law against different groups of citizens convey its key social values and priorities. Ultimately, this distribution will determine or seriously impact the levels of (in)equality within a country. Inequality can be as much—if not more—the result of economic laws and policies than of economic forces. Tax policies affect not only economic inequality but also gender, race, health, environmental, and political inequalities. These inequalities can also manifest as asymmetries, that is, different forms of inequality of information, power, access, and procedural position. These asymmetries, which are often overlooked due to their apparent invisibility and unmeasurable character, affect profoundly the ability of individuals to exercise their rights and overcome economic disparity. Digital technology has the potential of addressing many of these asymmetries, for example, by making information and education more accessible and creating new business opportunities that were once restricted to an economic elite. However, in the context of inclusion and inequality, digital technology is a double-edged sword which may empower some individuals while disempowering others. This thematic report makes a contribution to the debate on tax and inequalities, drawing on not only tax literature but also scholarship on administrative law, digital government, digital disconnects, datafication of the public administration, and the automation of administrative decision-making (including tax decisions). This report approaches the topic of tax and inequalities from a power asymmetry perspective (taxpayer vis-à-vis tax authority) and focuses on the digital context. The report is built around a number of concepts, including power, (in)equity, complexity, dependency, vulnerability, and digital divides. It discusses tax and inequalities adopting an administrative law lens, that is, the field that regulates the asymmetric interactions between citizens and public bodies (including tax authorities). The focus is on personal income tax and some of the benefits distributed by tax authorities such as childcare benefits. This report also pays special attention to the role of digitalization and automation of tax systems, examining how these technologies address traditional inequities while potentially creating new ones.